NPASS Natural Product

Natural Product: NPC475554

Natural Product ID:	NPC475554
Common Name:	Lyngbyabellin B
IUPAC Name:
Synonyms:
Molecular Formula:	C28H40Cl2N4O7S2
Standard InCHIKey:	XZRCVAJXDSWDNB-LWCVALJOSA-N
Standard InCHI:	InChI=1S/C28H40Cl2N4O7S2/c1-14(2)19-22-33-16(13-42-22)24(37)40-17(9-8-10-28(7,29)30)26(3,4)25(38)41-20(27(5,6)39)23-32-15(12-43-23)21(36)31-11-18(35)34-19/h13-15,17,19-20,39H,8-12H2,1-7H3,(H,31,36)(H,34,35)/t15-,17-,19-,20+/m0/s1
Canonical SMILES:	OC1=N[C@@H](C(C)C)c2scc(n2)C(=O)O[C@@H](CCCC(Cl)(Cl)C)C(C(=O)O[C@H](C2=N[C@H](C(=NC1)O)CS2)C(O)(C)C)(C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria				PMID[11076573]

Biological Activity

Activity Type	# Activity
EC50	1
IC50	5
LD50	1
Others	2

Activity Type	# Activity
Cell Line	6
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1917	Cell Line	CA46	Homo sapiens	Activity	=	28	%	18053715
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	710	nM	20055495
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	10.5	mm	22686608
NPT140	Organism	Artemia	Artemia	LD50	=	3	ppm	20100877
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.83	ug/ml	22583079
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.1	ug/ml	22583079
NPT2	Others	Unspecified		EC50	>	50000	nM	15711537
NPT1917	Cell Line	CA46	Homo sapiens	IC50	=	100	nM	17190454
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1100	nM	15686905

Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC475554 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	118
0.1-0.2	1669
0.2-0.3	17195
0.3-0.4	11010
0.4-0.5	775
0.5-0.6	56
0.6-0.7	57
0.7-0.8	3
0.8-0.85	0
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC132662
0.9057	High Similarity	NPC164006
0.8974	High Similarity	NPC216720
0.8917	High Similarity	NPC210424
0.8827	High Similarity	NPC134480
0.8773	High Similarity	NPC473704
0.7471	Intermediate Similarity	NPC56058
0.7471	Intermediate Similarity	NPC522
0.7301	Intermediate Similarity	NPC469801
0.6879	Remote Similarity	NPC267605
0.6813	Remote Similarity	NPC89592
0.6805	Remote Similarity	NPC475390
0.6795	Remote Similarity	NPC135558
0.6772	Remote Similarity	NPC51692
0.6646	Remote Similarity	NPC74917
0.6606	Remote Similarity	NPC120917
0.65	Remote Similarity	NPC312887
0.648	Remote Similarity	NPC127775
0.6457	Remote Similarity	NPC119481
0.6456	Remote Similarity	NPC214375
0.6444	Remote Similarity	NPC237219
0.6444	Remote Similarity	NPC231110
0.64	Remote Similarity	NPC473398
0.6389	Remote Similarity	NPC474538
0.6384	Remote Similarity	NPC475737
0.6384	Remote Similarity	NPC474094
0.6384	Remote Similarity	NPC185665
0.6384	Remote Similarity	NPC474067
0.6379	Remote Similarity	NPC319751
0.6348	Remote Similarity	NPC474090
0.6348	Remote Similarity	NPC154873
0.6348	Remote Similarity	NPC109498
0.6348	Remote Similarity	NPC163147
0.6348	Remote Similarity	NPC50274
0.6348	Remote Similarity	NPC252616
0.6348	Remote Similarity	NPC61667
0.6348	Remote Similarity	NPC45576
0.6348	Remote Similarity	NPC32583
0.6333	Remote Similarity	NPC21126
0.6324	Remote Similarity	NPC97078
0.6324	Remote Similarity	NPC470146
0.6324	Remote Similarity	NPC101980
0.6322	Remote Similarity	NPC190329
0.6313	Remote Similarity	NPC268063
0.6313	Remote Similarity	NPC224609
0.6286	Remote Similarity	NPC474069
0.6278	Remote Similarity	NPC202591
0.6278	Remote Similarity	NPC212214
0.6271	Remote Similarity	NPC82436
0.6271	Remote Similarity	NPC474103
0.6271	Remote Similarity	NPC474068
0.6271	Remote Similarity	NPC474064
0.6236	Remote Similarity	NPC21449
0.6236	Remote Similarity	NPC474079
0.6236	Remote Similarity	NPC475683
0.6236	Remote Similarity	NPC474080
0.6236	Remote Similarity	NPC474102
0.6236	Remote Similarity	NPC157194
0.6209	Remote Similarity	NPC52587
0.6167	Remote Similarity	NPC206724
0.6167	Remote Similarity	NPC474515
0.6164	Remote Similarity	NPC469858
0.608	Remote Similarity	NPC165538
0.6069	Remote Similarity	NPC103268
0.6061	Remote Similarity	NPC122427
0.6033	Remote Similarity	NPC315252
0.598	Remote Similarity	NPC329961
0.5954	Remote Similarity	NPC474070
0.5904	Remote Similarity	NPC222391
0.5895	Remote Similarity	NPC34319
0.5895	Remote Similarity	NPC256912
0.5895	Remote Similarity	NPC24990
0.5808	Remote Similarity	NPC137705
0.5798	Remote Similarity	NPC201014
0.5798	Remote Similarity	NPC110129
0.5795	Remote Similarity	NPC161242
0.5736	Remote Similarity	NPC25316
0.5736	Remote Similarity	NPC263485
0.5736	Remote Similarity	NPC229160
0.5728	Remote Similarity	NPC145178
0.5728	Remote Similarity	NPC475350
0.5728	Remote Similarity	NPC14877
0.5714	Remote Similarity	NPC476080
0.5714	Remote Similarity	NPC145047
0.5714	Remote Similarity	NPC86490
0.5714	Remote Similarity	NPC475534
0.5685	Remote Similarity	NPC475330
0.5657	Remote Similarity	NPC174652
0.5648	Remote Similarity	NPC251036
0.5638	Remote Similarity	NPC217981

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	100
0.1-0.2	614
0.2-0.3	3882
0.3-0.4	3999
0.4-0.5	543
0.5-0.6	18
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6503	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6907	Phase 2
0.6369	Remote Similarity	NPD6915	Approved
0.6333	Remote Similarity	NPD6910	Phase 3
0.6243	Remote Similarity	NPD6911	Discontinued
0.5939	Remote Similarity	NPD9579	Approved
0.5765	Remote Similarity	NPD2957	Phase 2

Structure

NPC475554 OpenBabel07101719522D 43 45 0 0 1 0 0 0 0 0999 V2000 -2.3853 -4.2838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5458 -3.1233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2234 1.6360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3516 1.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0127 0.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7674 -0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9096 0.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9633 0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3398 1.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5024 -3.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1633 -1.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8398 -1.5687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6306 -3.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7379 -2.2711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4343 -1.2404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5332 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0307 -3.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9606 -2.6985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4274 -0.3105 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4274 -2.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2711 -2.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7379 -0.7379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2711 -0.7379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5024 0.1633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0307 0.1633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0974 0.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2860 1.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2364 2.7340 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.8021 0.9930 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2949 -1.5045 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4343 -1.7686 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5332 -3.0090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1790 -4.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0974 -3.3685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1154 -0.3077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3542 1.0991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8522 1.2748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9606 -0.3105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7582 -2.0841 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.1633 -1.0307 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 28 1 0 0 0 0 11 18 1 0 0 0 0 11 31 1 0 0 0 0 12 43 1 0 0 0 0 13 16 2 0 0 0 0 13 42 1 0 0 0 0 15 12 1 1 0 0 0 15 21 1 0 0 0 0 15 32 1 0 0 0 0 16 24 1 0 0 0 0 16 33 1 0 0 0 0 17 9 1 1 0 0 0 17 26 1 0 0 0 0 17 40 1 0 0 0 0 18 34 2 3 0 0 0 18 35 1 0 0 0 0 19 14 1 1 0 0 0 19 22 1 0 0 0 0 19 34 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 1 0 0 0 20 41 1 0 0 0 0 21 31 2 3 0 0 0 21 36 1 0 0 0 0 22 33 2 0 0 0 0 22 42 1 0 0 0 0 23 32 2 0 0 0 0 23 43 1 0 0 0 0 24 37 2 0 0 0 0 24 40 1 0 0 0 0 25 26 1 0 0 0 0 25 38 2 0 0 0 0 25 41 1 0 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44558912
ChEMBL	CHEMBL508049
ZINC

Physicochemical Properties

Molecular Weight:	678.17
ALogP:	2.0488
MLogP:	2.89
XLogP:	3.824
# Rotatable Bonds:	18
Polar Surface Area:	216.8
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	43

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